Real Estate Investment Properties for Sale in Longwood, FL

Looking for investment property in Longwood, FL with high ROI ?

Explore a variety of short-term homes & houses in Longwood, FL. Invest wisely with VRBO & Longwood, FL Airbnb properties available for purchase. Find your ideal investment property among our curated listings for a rewarding real estate venture.

Investment Property for Sale in Longwood, FL

separator

PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
3996 RADLEY COURT #3996 Longwood, FL One or more photo(s) has been virtually staged. Do not miss this excellent opportunity to ...	2 beds \| 2 baths \| 1,427 sq.ft.	$225,000	Airbnb cash on cash: -1.76% Traditional cash on cash: 5.5% Airbnb Rental Income: $1115 Traditional Rental Income: $2287 Airbnb ROI: -1.76% Traditional ROI: 5.5%
4102 CLUBSIDE DRIVE #4102 Longwood, FL One or more photo(s) has been virtually staged. Spacious 2-Bedroom Corner Unit in Clubside...	2 beds \| 3 baths \| 1,380 sq.ft.	$220,000	Airbnb cash on cash: -1.39% Traditional cash on cash: 4.51% Airbnb Rental Income: $1115 Traditional Rental Income: $1969 Airbnb ROI: -1.39% Traditional ROI: 4.51%
417 SUMMIT RIDGE PLACE #213 Longwood, FL Welcome to this beautifully updated condo located in the desirable community, Residences a...	2 beds \| 2 baths \| 1,274 sq.ft.	$235,000	Airbnb cash on cash: -1.5% Traditional cash on cash: 3.59% Airbnb Rental Income: $1115 Traditional Rental Income: $1871 Airbnb ROI: -1.5% Traditional ROI: 3.59%
276 W BAY AVENUE Longwood, FL Step into the timeless elegance of this beautifully crafted Victorian Home, newer construc...	3 beds \| 3 baths \| 1,814 sq.ft.	$419,000	Airbnb cash on cash: 3.78% Traditional cash on cash: 3.8% Airbnb Rental Income: $3221 Traditional Rental Income: $2503 Airbnb ROI: 3.78% Traditional ROI: 3.8%
1665 GRANGE CIRCLE Longwood, FL Under contract-accepting backup offers. Expect to be impressed with this beautiful 3-bedro...	3 beds \| 2 baths \| 2,189 sq.ft.	$399,000	Airbnb cash on cash: 4.28% Traditional cash on cash: 6.3% Airbnb Rental Income: $3221 Traditional Rental Income: $3251 Airbnb ROI: 4.28% Traditional ROI: 6.3%
420 W WEKIVA TRAIL Longwood, FL Under contract-accepting backup offers. A RARE opportunity in Wekiva awaits! Every major u...	3 beds \| 2 baths \| 1,787 sq.ft.	$448,000	Airbnb cash on cash: 3.74% Traditional cash on cash: 3.16% Airbnb Rental Income: $3221 Traditional Rental Income: $2251 Airbnb ROI: 3.74% Traditional ROI: 3.16%
102 N SILVER CLUSTER COURT Longwood, FL Welcome to 102 Silver Cluster Ct N in Longwood, a beautifully maintained pool home under $...	3 beds \| 2 baths \| 1,166 sq.ft.	$383,000	Airbnb cash on cash: 4.63% Traditional cash on cash: 3.2% Airbnb Rental Income: $3221 Traditional Rental Income: $1980 Airbnb ROI: 4.63% Traditional ROI: 3.2%
1870 CROWLEY CIRCLE E Longwood, FL Short Sale. Welcome to your peacefull oasis located on a full acre. Spacious floor plan wi...	4 beds \| 4 baths \| 3,258 sq.ft.	$625,000	Airbnb cash on cash: 4.76% Traditional cash on cash: 5.32% Airbnb Rental Income: $5377 Traditional Rental Income: $4618 Airbnb ROI: 4.76% Traditional ROI: 5.32%
561 SHINING ARMOR LANE Longwood, FL Invest with success and buy through Auction.com. This bank-owned investment property is a ...	N/A beds \| N/A baths \| N/A	$358,000	Airbnb cash on cash: 2.29% Traditional cash on cash: 2.75% Airbnb Rental Income: $2039 Traditional Rental Income: $1664 Airbnb ROI: 2.29% Traditional ROI: 2.75%
884 CUTLER ROAD Longwood, FL One or more photo(s) has been virtually staged. Welcome to this beautifully updated 5-bedr...	5 beds \| 3 baths \| 2,601 sq.ft.	$615,000	Airbnb cash on cash: N/A Traditional cash on cash: 1.91% Airbnb Rental Income: $null Traditional Rental Income: $2235 Airbnb ROI: N/A Traditional ROI: 1.91%
105 DURHAM PLACE #105 Longwood, FL Discover 105 Durham Place, a 2-bedroom, 2-bathroom condo in the sought-after Wekiva commun...	2 beds \| 2 baths \| 1,427 sq.ft.	$250,000	Airbnb cash on cash: -1.69% Traditional cash on cash: 3.28% Airbnb Rental Income: $1115 Traditional Rental Income: $1914 Airbnb ROI: -1.69% Traditional ROI: 3.28%
413 WILLOWBROOK LANE Longwood, FL Under contract-accepting backup offers. One or more photo(s) has been virtually staged. Lo...	4 beds \| 2 baths \| 2,211 sq.ft.	$549,999	Airbnb cash on cash: 6.32% Traditional cash on cash: 5.12% Airbnb Rental Income: $5377 Traditional Rental Income: $3678 Airbnb ROI: 6.32% Traditional ROI: 5.12%
106 HIDDEN OAK DRIVE Longwood, FL Under contract-accepting backup offers. Tucked beneath a canopy of towering oaks on a quie...	3 beds \| 2 baths \| 2,127 sq.ft.	$460,000	Airbnb cash on cash: 3.42% Traditional cash on cash: 3.49% Airbnb Rental Income: $3221 Traditional Rental Income: $2525 Airbnb ROI: 3.42% Traditional ROI: 3.49%
478 SABAL TRAIL CIRCLE Longwood, FL PRICE ADJUSTMENT : Welcome to the desirable Sabal Point community! Located at 478 Sabal Tr...	4 beds \| 3 baths \| 2,529 sq.ft.	$629,900	Airbnb cash on cash: 4.94% Traditional cash on cash: 3.6% Airbnb Rental Income: $5377 Traditional Rental Income: $3502 Airbnb ROI: 4.94% Traditional ROI: 3.6%
105 FAIRWAY DRIVE Longwood, FL THE SPRINGS LIFESTYLE AT AN UNBEATABLE VALUE Imagine waking up in the heart of one of Lon...	2 beds \| 1 baths \| 1,140 sq.ft.	$170,000	Airbnb cash on cash: -1.68% Traditional cash on cash: 3.62% Airbnb Rental Income: $1115 Traditional Rental Income: $1600 Airbnb ROI: -1.68% Traditional ROI: 3.62%
300 NEW WATERFORD PLACE #202 Longwood, FL Perfect for First-Time Buyers or Those Ready to Downsize! Donât miss this rare opport...	2 beds \| 2 baths \| 1,176 sq.ft.	$269,900	Airbnb cash on cash: 0.67% Traditional cash on cash: 4.65% Airbnb Rental Income: $1115 Traditional Rental Income: $1754 Airbnb ROI: 0.67% Traditional ROI: 4.65%
114 JUNIPER LANE Longwood, FL Under contract-accepting backup offers. One or more photo(s) has been virtually staged. Qu...	2 beds \| 2 baths \| 2,049 sq.ft.	$460,000	Airbnb cash on cash: -0.39% Traditional cash on cash: 3.63% Airbnb Rental Income: $1115 Traditional Rental Income: $2469 Airbnb ROI: -0.39% Traditional ROI: 3.63%
308 SMOKERISE BOULEVARD Longwood, FL Under contract-accepting backup offers. Welcome to 308 Smokerise Blvd., tucked away on a q...	4 beds \| 2 baths \| 2,352 sq.ft.	$635,000	Airbnb cash on cash: 5.01% Traditional cash on cash: 3.46% Airbnb Rental Income: $5377 Traditional Rental Income: $3370 Airbnb ROI: 5.01% Traditional ROI: 3.46%
451 STANTON PLACE Longwood, FL Under contract-accepting backup offers. Welcome to Governorâs Point, a highly sought-aft...	3 beds \| 3 baths \| 1,682 sq.ft.	$334,900	Airbnb cash on cash: 3.82% Traditional cash on cash: 2.74% Airbnb Rental Income: $3221 Traditional Rental Income: $2154 Airbnb ROI: 3.82% Traditional ROI: 2.74%
860 Charlotte St. Longwood, FL 4-Bed / 3.5-Bath Home Built in 2006. -needs updating, new ac.	4 beds \| 4 baths \| N/A	$449,000	Airbnb cash on cash: 7.55% Traditional cash on cash: 5.25% Airbnb Rental Income: $5377 Traditional Rental Income: $3324 Airbnb ROI: 7.55% Traditional ROI: 5.25%
1025 BUCKSAW PLACE Longwood, FL Short Sale. Short Sale â Opportunity awaits! This home has been winterized and is ready ...	3 beds \| 3 baths \| 2,289 sq.ft.	$419,000	Airbnb cash on cash: 3.4% Traditional cash on cash: 6.1% Airbnb Rental Income: $3221 Traditional Rental Income: $3557 Airbnb ROI: 3.4% Traditional ROI: 6.1%
2040 E TRIANGLE DRIVE Longwood, FL Beautiful opportunity in the highly desirable Longwood area, perfectly located just minute...	3 beds \| 2 baths \| 1,283 sq.ft.	$340,000	Airbnb cash on cash: 5.42% Traditional cash on cash: 3.59% Airbnb Rental Income: $3221 Traditional Rental Income: $1912 Airbnb ROI: 5.42% Traditional ROI: 3.59%
1889 RANCHLAND TRAIL Longwood, FL Welcome to this beautifully renovated 4-bedroom, 3-bathroom pool home, perfectly situated ...	4 beds \| 3 baths \| 2,333 sq.ft.	$998,900	Airbnb cash on cash: 2.92% Traditional cash on cash: 2.18% Airbnb Rental Income: $5377 Traditional Rental Income: $3601 Airbnb ROI: 2.92% Traditional ROI: 2.18%
965 BUCKSAW PLACE Longwood, FL Under contract-accepting backup offers. Welcome to this spacious 4-bedroom, 3-bath home in...	4 beds \| 3 baths \| 2,361 sq.ft.	$530,000	Airbnb cash on cash: 6.13% Traditional cash on cash: 3.36% Airbnb Rental Income: $5377 Traditional Rental Income: $2919 Airbnb ROI: 6.13% Traditional ROI: 3.36%
305 SWEETWATER CLUB CIRCLE Longwood, FL Located behind the gates of the exclusive, guard-gated Sweetwater Club Tennis Community, t...	4 beds \| 6 baths \| 4,975 sq.ft.	$1,400,000	Airbnb cash on cash: 1.35% Traditional cash on cash: 4.21% Airbnb Rental Income: $5377 Traditional Rental Income: $8006 Airbnb ROI: 1.35% Traditional ROI: 4.21%
101 CHERRY HILL CIRCLE Longwood, FL This 4 bedrooms/3 bathrooms home is ideal for families and those who enjoy entertaining. R...	4 beds \| 3 baths \| 2,359 sq.ft.	$699,000	Airbnb cash on cash: 4.52% Traditional cash on cash: 2.49% Airbnb Rental Income: $5377 Traditional Rental Income: $2973 Airbnb ROI: 4.52% Traditional ROI: 2.49%
470 FREEMAN STREET Longwood, FL Set on an oversized lot with Water VIEWS in the desirable Longwood Plantation community, 4...	4 beds \| 2 baths \| 2,261 sq.ft.	$475,000	Airbnb cash on cash: 7.44% Traditional cash on cash: 4.75% Airbnb Rental Income: $5377 Traditional Rental Income: $3094 Airbnb ROI: 7.44% Traditional ROI: 4.75%
572 LAKE WILDMERE COVE Longwood, FL Here is your opportunity to own a true Turn Key Investment property.This almost new townho...	4 beds \| 5 baths \| 2,294 sq.ft.	$455,000	Airbnb cash on cash: 6.54% Traditional cash on cash: 3.79% Airbnb Rental Income: $5377 Traditional Rental Income: $3121 Airbnb ROI: 6.54% Traditional ROI: 3.79%
284 ISLAND SOUND COURT Longwood, FL Step into refined elegance and effortless sophistication in this nearly new Dockside maste...	4 beds \| 3 baths \| 2,692 sq.ft.	$799,999	Airbnb cash on cash: 3.56% Traditional cash on cash: 1.67% Airbnb Rental Income: $5377 Traditional Rental Income: $2884 Airbnb ROI: 3.56% Traditional ROI: 1.67%
486 N PIN OAK PLACE #112 Longwood, FL One or more photo(s) has been virtually staged. **Seller may consider buyer concessions if...	2 beds \| 1 baths \| 959 sq.ft.	$187,900	Airbnb cash on cash: 1.44% Traditional cash on cash: 7.19% Airbnb Rental Income: $1115 Traditional Rental Income: $1767 Airbnb ROI: 1.44% Traditional ROI: 7.19%
450 LONGMEADOW LANE Longwood, FL Excellent opportunity in Sabal Point. POOL house with two NEW HVACs. 4 bedrooms, 3.5 bathr...	4 beds \| 4 baths \| 2,623 sq.ft.	$539,000	Airbnb cash on cash: 6.54% Traditional cash on cash: 5.71% Airbnb Rental Income: $5377 Traditional Rental Income: $3873 Airbnb ROI: 6.54% Traditional ROI: 5.71%
556 LAKE WILDMERE COVE Longwood, FL MOTIVATED SELLER â MAJOR PRICE REDUCTION! Priced AGGRESSIVELY BELOW MARKET VALUE for an...	3 beds \| 3 baths \| 2,294 sq.ft.	$419,700	Airbnb cash on cash: 3.5% Traditional cash on cash: 5.09% Airbnb Rental Income: $3221 Traditional Rental Income: $3120 Airbnb ROI: 3.5% Traditional ROI: 5.09%
351 W HORNBEAM DRIVE Longwood, FL Under Construction. Welcome to one of the most exciting new builds to hit Longwood's covet...	4 beds \| 3 baths \| 2,778 sq.ft.	$750,000	Airbnb cash on cash: 4.59% Traditional cash on cash: -0.34% Airbnb Rental Income: $5377 Traditional Rental Income: $850 Airbnb ROI: 4.59% Traditional ROI: -0.34%
1310 RIDGE ROAD Longwood, FL Welcome to your own private oasis in the highly desirable Longwood area! This beautifully ...	3 beds \| 2 baths \| 1,520 sq.ft.	$475,000	Airbnb cash on cash: 3.46% Traditional cash on cash: 4.33% Airbnb Rental Income: $3221 Traditional Rental Income: $2881 Airbnb ROI: 3.46% Traditional ROI: 4.33%
803 SWEETWATER CLUB BOULEVARD Longwood, FL One or more photo(s) has been virtually staged. In the heart of the coveted, gated Sweetwa...	4 beds \| 6 baths \| 5,344 sq.ft.	$1,575,000	Airbnb cash on cash: 0.72% Traditional cash on cash: 3.68% Airbnb Rental Income: $5377 Traditional Rental Income: $8614 Airbnb ROI: 0.72% Traditional ROI: 3.68%
322 N SHADOWBAY BOULEVARD Longwood, FL Back on the Market! Welcome to Lake Vista at Shadowbay, a highly desirable community with ...	3 beds \| 2 baths \| 1,599 sq.ft.	$499,900	Airbnb cash on cash: 3.64% Traditional cash on cash: 4.42% Airbnb Rental Income: $3221 Traditional Rental Income: $2858 Airbnb ROI: 3.64% Traditional ROI: 4.42%
123 TOMOKA TRAIL #123 Longwood, FL True Florida Paradise ! Possible owner financing is just an added bonus True gated and gua...	2 beds \| 2 baths \| 1,243 sq.ft.	$249,900	Airbnb cash on cash: 0.86% Traditional cash on cash: 7.34% Airbnb Rental Income: $1115 Traditional Rental Income: $2269 Airbnb ROI: 0.86% Traditional ROI: 7.34%
307 COBLE DRIVE Longwood, FL Some homes just feel right the moment you walk inâ¦ and 307 Coble Drive is one of them. ...	4 beds \| 2 baths \| 1,987 sq.ft.	$475,000	Airbnb cash on cash: 7.19% Traditional cash on cash: 4.8% Airbnb Rental Income: $5377 Traditional Rental Income: $3230 Airbnb ROI: 7.19% Traditional ROI: 4.8%
420 SUMMIT RIDGE PLACE #200 Longwood, FL **This property qualifies for a closing cost credit up to $3,700 through the Sellerâs pr...	3 beds \| 2 baths \| 1,586 sq.ft.	$219,000	Airbnb cash on cash: 6.19% Traditional cash on cash: 6.21% Airbnb Rental Income: $3221 Traditional Rental Income: $2499 Airbnb ROI: 6.19% Traditional ROI: 6.21%
2745 Night Hawk Ct. Longwood, FL Don't miss out on this opportunity to own a 3 bedroom, 2 bath townhouse in Shadowbay Club....	3 beds \| 2 baths \| 1,396 sq.ft.	$335,000	Airbnb cash on cash: 5.43% Traditional cash on cash: 5.14% Airbnb Rental Income: $3221 Traditional Rental Income: $2403 Airbnb ROI: 5.43% Traditional ROI: 5.14%

Real Estate investment in Longwood, FL

There are 128 properties for sale in the city of Longwood . The median list price in Longwood is $449,000 and the average price per square foot is $213. In June 2026, the average monthly cash on cash return in Longwood is 4.00%. The average monthly rental income in Longwood is $2,403.

Longwood, FL Real Estate Investing: FAQs for Buyers, Sellers and Investors

There are 128 investment properties available for sale in Longwood.

In 2026, the best neighborhood to buy investment property is Longwood.

The ROI for Short-Term is higher than the Long-Term in Longwood with average rental income of $3,221.

Your search for investment property begins and ends here

Investment Property for Sale in Longwood, FL

3996 RADLEY COURT #3996

Longwood, FL

2 beds | 2 baths | 1,427 sq.ft.

$225,000

Airbnb cash on cash: -1.76%

Traditional cash on cash: 5.5%

Airbnb Rental Income: $1115

Traditional Rental Income: $2287

Airbnb ROI: -1.76%

Traditional ROI: 5.5%

4102 CLUBSIDE DRIVE #4102

Longwood, FL

2 beds | 3 baths | 1,380 sq.ft.

$220,000

Airbnb cash on cash: -1.39%

Traditional cash on cash: 4.51%

Airbnb Rental Income: $1115

Traditional Rental Income: $1969

Airbnb ROI: -1.39%

Traditional ROI: 4.51%

417 SUMMIT RIDGE PLACE #213

Longwood, FL

2 beds | 2 baths | 1,274 sq.ft.

$235,000

Airbnb cash on cash: -1.5%

Traditional cash on cash: 3.59%

Airbnb Rental Income: $1115

Traditional Rental Income: $1871

Airbnb ROI: -1.5%

Traditional ROI: 3.59%

276 W BAY AVENUE

Longwood, FL

3 beds | 3 baths | 1,814 sq.ft.

$419,000

Airbnb cash on cash: 3.78%

Traditional cash on cash: 3.8%

Airbnb Rental Income: $3221

Traditional Rental Income: $2503

Airbnb ROI: 3.78%

Traditional ROI: 3.8%

1665 GRANGE CIRCLE

Longwood, FL

3 beds | 2 baths | 2,189 sq.ft.

$399,000

Airbnb cash on cash: 4.28%

Traditional cash on cash: 6.3%

Airbnb Rental Income: $3221

Traditional Rental Income: $3251

Airbnb ROI: 4.28%

Traditional ROI: 6.3%

420 W WEKIVA TRAIL

Longwood, FL

3 beds | 2 baths | 1,787 sq.ft.

$448,000

Airbnb cash on cash: 3.74%

Traditional cash on cash: 3.16%

Airbnb Rental Income: $3221

Traditional Rental Income: $2251

Airbnb ROI: 3.74%

Traditional ROI: 3.16%

102 N SILVER CLUSTER COURT

Longwood, FL

3 beds | 2 baths | 1,166 sq.ft.

$383,000

Airbnb cash on cash: 4.63%

Traditional cash on cash: 3.2%

Airbnb Rental Income: $3221

Traditional Rental Income: $1980

Airbnb ROI: 4.63%

Traditional ROI: 3.2%

1870 CROWLEY CIRCLE E

Longwood, FL

4 beds | 4 baths | 3,258 sq.ft.

$625,000

Airbnb cash on cash: 4.76%

Traditional cash on cash: 5.32%

Airbnb Rental Income: $5377

Traditional Rental Income: $4618

Airbnb ROI: 4.76%